Incident #236: No Walk In The Park (with Dakota)

Every blue moon, we receive a newly minted adult into our Halfway House from a facility for the younger delinquents. It’s a mixed bag with these guys: sometimes they are already hardened to the ways of institutionalization, and sometimes they are like a young buck in a fresh green meadow. Usually they are covered in jailhouse tats, and have adopted the prison-chic clothing so loved by those school-to-prison pipeline types. This resident, however, was unlike the others. He had such an innocent look about him, you’d never guess half the shit on his rap sheet. Lucky for him, that rap sheet isn’t going to become public, and thus, he has a real chance to start again from scratch. When I called him into the bedroom and asked him to set down, you’d think he was in the principal’s office. He looked worried, and like he might start crying any moment. While that was sort of endearing, I nevertheless was brusque with him while he was reading and signing the rules of the House. Although he looked innocent, I knew that he was just a used up dirty bitch like all the others; I decided to get my cock wet with him before he started causing any trouble. I must admit, his little 18 year old lips felt nice wrapped around my dick, and he didn’t seem to have much of a gag reflex. But the hottest part of the blowjob was just him staring up at me with those pretty blue eyes of his. He was desperately seeking approval, and you could tell it. I hadn’t even stuck my cock in his fuck hole and I could already tell he was going to be my new favorite piece of fuck meat. When I had him lube up my dick and stick it in himself, he slowly but gently let the head of my cock pop into his sphincter, and from that point on it was a go. He didn’t need much loosening up, which made me wonder how many times he had been in this situation. His ass was so smooth and silky that it told me, “A lot of times,” but the expression on his face told another story. Never in my life had I been fucking a resident who had such a dumbfounded look on his face. Who knows, maybe he thought that it all gets better once you turn 18. I hated to break it to him, but for his type it only gets worse. To finish off, since his ass felt so damn good I had him ride me, at first facing me, and then facing away. Given the baby fat and not very muscular body, I was surprised that his legs didn’t give out sooner. Sure enough, he rode that dick until I popped deep inside of him. What a people pleaser this young resident is! I bet his legs were sore the next day, though, not to mention his ass. When I smacked him good on his way out the door, his astonishment was palpable. It’s nice to have a teen like this around, for sure. Even though it’s no walk in the park, this job definitely has its perks!